CA2858755C - Composition d'additif destinee au controle et a l'inhibition de la polymerisation de monomeres vinyliques aromatiques, et sa methode d'utilisation - Google Patents
Composition d'additif destinee au controle et a l'inhibition de la polymerisation de monomeres vinyliques aromatiques, et sa methode d'utilisation Download PDFInfo
- Publication number
- CA2858755C CA2858755C CA2858755A CA2858755A CA2858755C CA 2858755 C CA2858755 C CA 2858755C CA 2858755 A CA2858755 A CA 2858755A CA 2858755 A CA2858755 A CA 2858755A CA 2858755 C CA2858755 C CA 2858755C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- amine
- aliphatic tertiary
- additive composition
- tertiary amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 172
- 239000000654 additive Substances 0.000 title claims abstract description 82
- 230000000996 additive effect Effects 0.000 title claims abstract description 81
- 239000000178 monomer Substances 0.000 title claims abstract description 80
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 66
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 43
- 230000005764 inhibitory process Effects 0.000 title abstract description 33
- -1 aromatic nitro compounds Chemical class 0.000 claims abstract description 154
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 128
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 16
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims description 77
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 58
- 150000001412 amines Chemical class 0.000 claims description 39
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 28
- 150000003512 tertiary amines Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 18
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 14
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 14
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 14
- 229940043237 diethanolamine Drugs 0.000 claims description 14
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 14
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 11
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 9
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- KKZZSTCINUMTGD-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidin-4-ol Chemical compound CC1C(O)CCN(C)C1(C)C KKZZSTCINUMTGD-UHFFFAOYSA-N 0.000 claims description 4
- 229940012017 ethylenediamine Drugs 0.000 claims description 4
- BYACHAOCSIPLCM-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol Chemical group OCCN(CCO)CCN(CCO)CCO BYACHAOCSIPLCM-UHFFFAOYSA-N 0.000 claims description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 2
- KSHJAFFDLKPUMT-UHFFFAOYSA-N dinitro-ortho-cresol Chemical compound CC1=C(O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KSHJAFFDLKPUMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 12
- 229920000642 polymer Polymers 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing a phenol or quinone moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/42—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using short-stopping agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen
- C09K15/18—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen containing an amine or imine moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention concerne une composition d'additif améliorée pour la régulation et l'inhibition de la polymérisation de monomères vinylaromatiques notamment du styrène, comprenant un ou plusieurs composés aromatiques nitro, et une ou plusieurs amines tertiaires aliphatiques. Dans un mode de mise en uvre, la présente invention concerne en outre un procédé d'utilisation de ladite composition. Dans un autre mode de mise en uvre, la présente invention concerne un procédé permettant de réguler et d'inhiber la polymérisation de monomères vinylaromatiques tels que le styrène, par l'utilisation de ladite composition. Dans un mode de mise en uvre encore différent, la présente invention concerne un procédé de préparation de ladite composition.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3461/MUM/2011 | 2011-12-09 | ||
| IN3461MU2011 | 2011-12-09 | ||
| PCT/IN2012/000785 WO2013108266A1 (fr) | 2011-12-09 | 2012-12-03 | Composition d'additif améliorée pour la régulation et l'inhibition de la polymérisation de monomères vinylaromatiques, et procédé d'utilisation de cette composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2858755A1 CA2858755A1 (fr) | 2013-07-25 |
| CA2858755C true CA2858755C (fr) | 2016-08-23 |
Family
ID=54258976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2858755A Active CA2858755C (fr) | 2011-12-09 | 2012-12-03 | Composition d'additif destinee au controle et a l'inhibition de la polymerisation de monomeres vinyliques aromatiques, et sa methode d'utilisation |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9228126B2 (fr) |
| EP (1) | EP2788303B1 (fr) |
| JP (2) | JP2015504857A (fr) |
| KR (1) | KR102033096B1 (fr) |
| CN (1) | CN104302602B (fr) |
| AU (1) | AU2012366691B2 (fr) |
| BR (1) | BR112014013855B1 (fr) |
| CA (1) | CA2858755C (fr) |
| ES (1) | ES2548554T3 (fr) |
| MX (1) | MX338697B (fr) |
| MY (1) | MY168418A (fr) |
| PH (1) | PH12014501270B1 (fr) |
| PL (1) | PL2788303T3 (fr) |
| RU (1) | RU2612511C2 (fr) |
| SG (1) | SG11201403026XA (fr) |
| TW (1) | TWI582065B (fr) |
| WO (1) | WO2013108266A1 (fr) |
| ZA (1) | ZA201404987B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015504857A (ja) | 2011-12-09 | 2015-02-16 | ドルフ ケタール ケミカルズ（インド）プライベート リミテッドＤｏｒｆ Ｋｅｔａｌ Ｃｈｅｍｉｃａｌｓ（Ｉｎｄｉａ） Ｐｒｉｖａｔｅ Ｌｉｍｉｔｅｄ | 芳香族ビニルモノマーの重合を制御及び阻害する改善された添加剤組成物、及びその使用方法 |
| RU2612514C2 (ru) * | 2011-12-26 | 2017-03-09 | Дорф Кетал Кемикалс (Индия) Прайвит Лимитэд | Усовершенствованная композиция добавки на основе амина для контроля и ингибирования полимеризации ароматических виниловых мономеров и способ ее использования |
| IN2013MU01165A (fr) * | 2013-03-26 | 2015-04-24 | Dorf Ketal Chemicals India Private Ltd | |
| EP3400087B1 (fr) * | 2016-01-05 | 2020-02-19 | Dorf Ketal Chemicals (India) Private Limited | Composition d'additif de fixation de sulfure d'hydrogène et procédé d'utilisation associé |
| EP3820836A1 (fr) | 2018-07-13 | 2021-05-19 | Ecolab USA, Inc. | Compositions d'amines oxygénées et de méthides de quinone en tant qu'agents anti-salissures pour monomères vinyliques |
| ES2971105T3 (es) | 2018-07-13 | 2024-06-03 | Ecolab Usa Inc | Composición para inhibir la polimerización de monómeros que comprende un inhibidor de nitróxido, un retardante de metida de quinona y un estabilizador de amina |
| EP4036074A1 (fr) | 2021-01-27 | 2022-08-03 | Evonik Operations GmbH | Procédé de suppression de la polymérisation de monomères aromatiques insaturés |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3808184A (en) * | 1972-06-14 | 1974-04-30 | Universal Pvc Resins | Method of reducing polymerization of vinyl chloride in a monomer recovery system |
| US4105506A (en) * | 1977-02-24 | 1978-08-08 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
| US4466905A (en) * | 1983-04-11 | 1984-08-21 | Cosden Technology, Inc. | Polymerization inhibition process for vinyl aromatic compounds |
| EP0240297A1 (fr) | 1986-04-01 | 1987-10-07 | Betz Europe, Inc. | Procédé pour inhiber la polymérisation de composés vinylaromatiques |
| JPS62280285A (ja) * | 1986-05-29 | 1987-12-05 | Dia Furotsuku Kk | 改良された樹脂含浸剤組成物 |
| US5254760A (en) | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US6403850B1 (en) * | 2000-01-18 | 2002-06-11 | Uniroyal Chemical Company, Inc. | Inhibition of polymerization of unsaturated monomers |
| US6685823B2 (en) * | 2000-10-16 | 2004-02-03 | Uniroyal Chemical Company, Inc. | C-nitrosoaniline compounds and their blends as polymerization inhibitors |
| US20040034247A1 (en) * | 2002-08-16 | 2004-02-19 | Sherif Eldin | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| JP4319565B2 (ja) * | 2004-03-02 | 2009-08-26 | 伯東株式会社 | 重合抑制方法。 |
| RU2378242C2 (ru) * | 2004-09-28 | 2010-01-10 | Кемтура Корпорейшн | Сульфированные нитрофенолы в качестве ингибиторов полимеризации |
| JP4679144B2 (ja) * | 2004-12-28 | 2011-04-27 | 伯東株式会社 | ジビニルベンゼンと、スチレン又はスチレン誘導体を含む共重合体の重合抑制方法 |
| US8246858B2 (en) * | 2006-03-24 | 2012-08-21 | Hakuto Co., Ltd. | Process for inhibiting polymerization of an aromatic vinyl compound |
| US7651635B1 (en) * | 2009-02-05 | 2010-01-26 | Nalco Company | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxylamine combination |
| JP5585333B2 (ja) * | 2010-09-14 | 2014-09-10 | ユニマテック株式会社 | フルオロアルキルビニルエーテルの重合抑制方法 |
| AU2012322294B2 (en) * | 2011-08-26 | 2016-04-14 | Dorf Ketal Chemicals (India) Private Limited | Additive composition for control and inhibition of polymerization of styrene, and method of preparation and use thereof |
| US9206268B2 (en) * | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
| JP2015504857A (ja) | 2011-12-09 | 2015-02-16 | ドルフ ケタール ケミカルズ（インド）プライベート リミテッドＤｏｒｆ Ｋｅｔａｌ Ｃｈｅｍｉｃａｌｓ（Ｉｎｄｉａ） Ｐｒｉｖａｔｅ Ｌｉｍｉｔｅｄ | 芳香族ビニルモノマーの重合を制御及び阻害する改善された添加剤組成物、及びその使用方法 |
-
2012
- 2012-12-03 JP JP2014545452A patent/JP2015504857A/ja active Pending
- 2012-12-03 MX MX2014006924A patent/MX338697B/es active IP Right Grant
- 2012-12-03 US US14/363,743 patent/US9228126B2/en active Active
- 2012-12-03 RU RU2014127330A patent/RU2612511C2/ru active
- 2012-12-03 CA CA2858755A patent/CA2858755C/fr active Active
- 2012-12-03 WO PCT/IN2012/000785 patent/WO2013108266A1/fr active Application Filing
- 2012-12-03 ES ES12839192.7T patent/ES2548554T3/es active Active
- 2012-12-03 BR BR112014013855-9A patent/BR112014013855B1/pt active IP Right Grant
- 2012-12-03 SG SG11201403026XA patent/SG11201403026XA/en unknown
- 2012-12-03 PL PL12839192T patent/PL2788303T3/pl unknown
- 2012-12-03 EP EP12839192.7A patent/EP2788303B1/fr active Active
- 2012-12-03 MY MYPI2014001664A patent/MY168418A/en unknown
- 2012-12-03 CN CN201280060696.6A patent/CN104302602B/zh active Active
- 2012-12-03 AU AU2012366691A patent/AU2012366691B2/en not_active Ceased
- 2012-12-03 KR KR1020147015334A patent/KR102033096B1/ko active IP Right Grant
- 2012-12-07 TW TW101146119A patent/TWI582065B/zh active
-
2014
- 2014-06-05 PH PH12014501270A patent/PH12014501270B1/en unknown
- 2014-07-08 ZA ZA2014/04987A patent/ZA201404987B/en unknown
-
2016
- 2016-08-25 JP JP2016164537A patent/JP6190930B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| PH12014501270A1 (en) | 2014-09-08 |
| EP2788303B1 (fr) | 2015-07-15 |
| MX2014006924A (es) | 2014-09-08 |
| WO2013108266A1 (fr) | 2013-07-25 |
| CA2858755A1 (fr) | 2013-07-25 |
| JP2015504857A (ja) | 2015-02-16 |
| US9228126B2 (en) | 2016-01-05 |
| KR102033096B1 (ko) | 2019-10-16 |
| MY168418A (en) | 2018-11-09 |
| EP2788303A1 (fr) | 2014-10-15 |
| TWI582065B (zh) | 2017-05-11 |
| CN104302602B (zh) | 2017-03-08 |
| PH12014501270B1 (en) | 2014-09-08 |
| RU2612511C2 (ru) | 2017-03-09 |
| CN104302602A (zh) | 2015-01-21 |
| US20140350313A1 (en) | 2014-11-27 |
| ES2548554T3 (es) | 2015-10-19 |
| BR112014013855B1 (pt) | 2020-11-17 |
| SG11201403026XA (en) | 2014-07-30 |
| RU2014127330A (ru) | 2016-02-10 |
| JP2017036284A (ja) | 2017-02-16 |
| ZA201404987B (en) | 2016-08-31 |
| AU2012366691A1 (en) | 2014-07-24 |
| KR20140100949A (ko) | 2014-08-18 |
| MX338697B (es) | 2016-04-28 |
| WO2013108266A4 (fr) | 2013-10-10 |
| AU2012366691B2 (en) | 2015-07-02 |
| TW201331159A (zh) | 2013-08-01 |
| PL2788303T3 (pl) | 2015-12-31 |
| JP6190930B2 (ja) | 2017-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140609 |